4,7-Dichloroquinoline → 7-chloro-4-(2,5-dimethyl-1H-indol-3-yl)quinoline

HRID 418421

Reaktionsgleichung

Reaktionsgleichung von HRID 418421
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([CH3:11])=[CH:6][CH:5]=2.CC[Mg+].[Br-].Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=2)[N:20]=[CH:19][CH:18]=1.CCOC(C)=O>C1(C)C=CC=CC=1.C1COCC1.O>[Cl:27][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([CH3:11])[CH:8]=4)[NH:3][C:2]=3[CH3:1])=[CH:18][CH:19]=[N:20]2)=[CH:25][CH:24]=1

Komponenten

8

Edukt 4

HCID 68664,7-DichloroquinolineHCID 8857Ethyl AcetateHCID 709652,5-Dimethyl-1H-indoleHCID 178461630HCID 178461630, Verbindung

Produkt 1

HCID 111625767-chloro-4-(2,5-dimethyl-1H-indol-3-yl)quinolineAusbeute 44,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2,5-dimethylindole (500 mg) was dissolved in dry toluene (2 ml), and maintained under a nitrogen atmosphere. The reaction was cooled to 0° C. before adding EtMgBr (2.5 ml, 3M in Et2O) dropwise, keeping the temperature below 5° C. Allowed the mixture to warm to RT and stirred for 0.5 h. A solution of 4,7-dichloroquinoline (680 mg) in dry THF (3 ml) was added slowly to the reaction. After stirring for 30 minutes at RT the reaction was slowly heated to 90° C. and stirred overnight. The reaction was allowed to cool to RT before adding EtOAc and water to the mixture. The organic layer was separated and the organic layer was extracted with EtOAc (×3). The combined organics were washed with saturated aqueous NH4Cl, H2O and brine then dried (Na2SO4) and the solvent was evaporated under reduced pressure. Purification by chromatography eluting with 15% acetone/isohexane gave the sub-title compound (0.47 g).

Aufarbeitung

  1. temperaturemaintained under a nitrogen atmosphere
  2. customthe temperature below 5° C
  3. temperatureAllowed the mixture to warm to RT
  4. stirringAfter stirring for 30 minutes at RT the reaction
  5. temperaturewas slowly heated to 90° C.
  6. stirringstirred overnight
  7. temperatureto cool to RT
  8. customThe organic layer was separated
  9. extractionthe organic layer was extracted with EtOAc (×3)
  10. washThe combined organics were washed with saturated aqueous NH4Cl, H2O and brine
  11. dry with materialthen dried (Na2SO4)
  12. customthe solvent was evaporated under reduced pressure
  13. customPurification by chromatography
  14. washeluting with 15% acetone/isohexane

Quellen und Nachweise

ORD-Eintrag
ord-ba5861c21f774af2848a3b9d98b50992
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093278B2

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